Pyridine → Tert-butyl 2,6-dichloropyrimidine-4-carboxylate

HRID 1752395Notes

Reaction equation

HRID 1752395 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1.CCN(C(C)C)C(C)C.[C:21]([OH:25])([CH3:24])([CH3:23])[CH3:22].N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 110311332,6-dichloropyrimidine-4-carbonyl Chloride

Product 1

HCID 57285994Tert-butyl 2,6-dichloropyrimidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dichloropyrimidine-4-carbonyl chloride (1.026 g, 4.85 mmol) in DCM (25 mL) was added iPr2NEt (1.01 mL, 5.80 mmol) and t-butanol (0.51 mL, 5.3 mmol). The mixture was stirred overnight then pyridine (0.39 mL, 4.8 mmol) was added and the stirring continued over another night. The reaction mixture was evaporated in vacuo and the resulting residue was chromatographed over silica gel with 0-40% EtOAc in hexanes. The product fractions were evaporated in vacuo to give tert-butyl 2,6-dichloropyrimidine-4-carboxylate as a yellow-orange waxy solid (0.310 g, 1.24 mmol, 26% yield). 1H NMR (400 MHz, DMSO-d6): 8.15 (1H, s), 1.56 (9H, s). LC/MS: m/z=271.1 [M+Na]+.

Workup

  1. waitthe stirring continued over another night
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe resulting residue was chromatographed over silica gel with 0-40% EtOAc in hexanes
  4. customThe product fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-a135bad77da44fc996a1753a5d5a3b6e
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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